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P4405 Sigma

Podophyllotoxin

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Description

Biochem/physiol Actions

Inhibits microtubule assembly; antineoplastic.

Packaging

100 mg in glass bottle

50 mg in poly bottle

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

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Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3462 6.1 / PGII
WGK Germany 
3
RTECS 
LV2500000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles
Peer-Reviewed Papers

References

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Podophyllotoxins: current status and recent developments. Damayanthi, Y. and Lown, J.W. Curr. Med. Chem. 5, 205, (1998)

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Podophyllotoxin and nocodazole counter the effect of IKP104 on tubulin decay. Prasad, V., et al. J. Protein Chem. 17, 663, (1998)

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A highly tumor-targeted nanoparticle of podophyllotoxin penetrated tumor core and regressed multidrug resistant tumors. Roy A, Ernsting MJ, Undzys E, et al. Biomaterials 52, 335-46, (2015)

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Dual extraction of essential oil and podophyllotoxin from creeping juniper (Juniperus horizontalis). Cantrell CL, Zheljazkov VD, Carvalho CR, et al. PLoS ONE 9(9), e106057, (2014)

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Anti-Helicobacter pylori, gastroprotective, anti-inflammatory, and cytotoxic activities of methanolic extracts of five different populations of Hippocratea celastroides collected in Mexico. Hinojosa WI, Quiróz MA, Álvarez IR, et al. J. Ethnopharmacol. 155(2), 1156-63, (2014)

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Transcriptome sequencing of rhizome tissue of Sinopodophyllum hexandrum at two temperatures. Kumari A, Singh HR, Jha A, et al. BMC Genomics 15, 871, (2014)

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Synthesis and antitumor activity of novel per-butyrylated glycosides of podophyllotoxin and its derivatives. Zi CT, Yang D, Dong FW, et al. Bioorg. Med. Chem. 23(7), 1437-46, (2015)

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Study of cytotoxic activity, podophyllotoxin, and deoxypodophyllotoxin content in selected Juniperus species cultivated in Poland. Och M, Och A, Cie?la ?, et al. Pharm. Biol. 53(6), 831-7, (2015)

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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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Synthesis and antiprotozoal activity of cationic 1,4-diphenyl-1H-1,2,3-triazoles. Stanislav A Bakunov et al J. Med. Chem. 53, 254-72, (2010)

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Antimalarial ?-carbolines from the New Zealand ascidian Pseudodistoma opacum. Susanna T S Chan et al J. Nat. Prod. 74, 1972-9, (2011)

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Didemnidines A and B, indole spermidine alkaloids from the New Zealand ascidian Didemnum sp. Rhys Finlayson et al J. Nat. Prod. 74, 888-92, (2011)

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Antiprotozoal steroidal saponins from the marine sponge Pandaros acanthifolium. Erik L Regalado et al J. Nat. Prod. 73, 1404-10, (2010)

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Trypanothione reductase high-throughput screening campaign identifies novel classes of inhibitors with antiparasitic activity. Georgina A Holloway et al Antimicrob. Agents Chemother. 53, 2824-33, (2009)

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Antitrypanosomal activity of 1,2-dihydroquinolin-6-ols and their ester derivatives. Jean Fotie et al J. Med. Chem. 53, 966-82, (2010)

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Structure-activity study of pentamidine analogues as antiprotozoal agents. Svetlana M Bakunova et al J. Med. Chem. 52, 2016-35, (2009)

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Synthesis and in vitro antiprotozoal activities of dicationic 3,5-diphenylisoxazoles. Donald A Patrick et al J. Med. Chem. 50, 2468-85, (2007)

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Isoneocryptolepine, a synthetic indoloquinoline alkaloid, as an antiplasmodial lead compound. Sabine Van Miert et al J. Nat. Prod. 68, 674-7, (2005)

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Acyclic nucleoside analogues as inhibitors of Plasmodium falciparum dUTPase. Corinne Nguyen et al J. Med. Chem. 49, 4183-95, (2006)

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Synthesis and in vitro antiprotozoal activity of bisbenzofuran cations. Svetlana M Bakunova et al J. Med. Chem. 50, 5807-23, (2007)

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Limonoid orthoacetates and antiprotozoal compounds from the roots of Pseudocedrela kotschyi. Anne-Emmanuelle Hay et al J. Nat. Prod. 70, 9-13, (2007)

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Synthesis and antiprotozoal activity of cationic 2-phenylbenzofurans. Stanislav A Bakunov et al J. Med. Chem. 51, 6927-44, (2008)

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Marine natural products from the Turkish sponge Agelas oroides that inhibit the enoyl reductases from Plasmodium falciparum, Mycobacterium tuberculosis and Escherichia coli. Deniz Tasdemir et al Bioorg. Med. Chem. 15, 6834-45, (2007)

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Synthesis and evaluation of antiparasitic activities of new 4-[5-(4-phenoxyphenyl)-2H-pyrazol-3-yl]morpholine derivatives. Sabine Kuettel et al J. Med. Chem. 50, 5833-9, (2007)

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Antiprotozoal activities of heterocyclic-substituted xanthones from the marine-derived fungus Chaetomium sp. Alexander Pontius et al J. Nat. Prod. 71, 1579-84, (2008)

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Antimalarial Pyrido[1,2-a]benzimidazoles A. J. Ndakala, et al., J. Med. Chem. 54, 4581-4589, (2011)

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Quinuclidine derivatives as potential antiparasitics. Simon B Cammerer et al Antimicrob. Agents Chemother. 51, 4049-61, (2007)

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Synthesis and anti-protozoal activity of novel dihydropyrrolo[3,4-d][1,2,3]triazoles. Ya?ar Dürüst et al Eur. J. Med. Chem. 48, 296-304, (2012)

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End-binding proteins sensitize microtubules to the action of microtubule-targeting agents. Mohan R, Katrukha EA, Doodhi H, et al. Proc. Natl. Acad. Sci. U. S. A. 110(22), 8900-5, (2013)

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Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues. Van Baelen, G., et al. Bioorg. Med. Chem. 17, 7209-7217, (2009)

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Compounds structurally related to ellagic acid show improved antiplasmodial activity. Nicole Sturm et al Antimicrob. Agents Chemother. 53, 622-30, (2009)

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Synthesis and antimalarial and antituberculosis activities of a series of natural and unnatural 4-methoxy-6-styryl-pyran-2-ones, dihydro analogues and photo-dimers. Stephen T McCracken et al Bioorg. Med. Chem. 20, 1482-93, (2012)

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Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines. Romina J Pagliero et al Bioorg. Med. Chem. 18, 142-50, (2010)

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Antiprotozoal polyacetylenes from the Tanzanian medicinal plant Cussonia zimmermannii. Martin Senn et al J. Nat. Prod. 70, 1565-9, (2007)

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GS-9191 is a novel topical prodrug of the nucleotide analog 9-(2-phosphonylmethoxyethyl)guanine with antiproliferative activity and possible utility in the treatment of human papillomavirus lesions. Grushenka H I Wolfgang et al Antimicrob. Agents Chemother. 53, 2777-84, (2009)

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Synthesis and antiparasitic and antifungal evaluation of 2'-arylsubstituted-1H,1'H-[2,5']bisbenzimidazolyl-5-carboxamidines. Mehmet Alp et al Eur. J. Med. Chem. 44, 2002-8, (2009)

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Synthesis and antitrypanosomal evaluation of derivatives of N-benzyl-1,2-dihydroquinolin-6-ols: Effect of core substitutions and salt formation. Carolyn S Reid et al Bioorg. Med. Chem. 19, 513-23, (2011)

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Synthesis and antiprotozoal activity of pyridyl analogues of pentamidine. Svetlana M Bakunova et al J. Med. Chem. 52, 4657-67, (2009)

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Antiparasitic compounds from Cupania cinerea with activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense. M Salomé Gachet et al J. Nat. Prod. 74, 559-66, (2011)

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Synthesis and in vitro antiprotozoal activities of water-soluble, inexpensive 3,7-bis(dialkylamino)phenoxazin-5-ium derivatives. Jian-Feng Ge et al J. Med. Chem. 51, 3654-8, (2008)

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Condyloma eradication: self-therapy with 0.15-0.5% podophyllotoxin versus 20-25% podophyllin preparations--an integrated safety assessment. Longstaff E and von Krogh G Regul Toxicol Pharmacol 33(2), 117-37, (2001)

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2-Hexadecynoic acid inhibits plasmodial FAS-II enzymes and arrests erythrocytic and liver stage Plasmodium infections. Deniz Tasdemir et al Bioorg. Med. Chem. 18, 7475-85, (2010)

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Antiplasmodial and cytotoxicity evaluation of 3-functionalized 2-azetidinone derivatives. Pardeep Singh et al Bioorg. Med. Chem. Lett. 21, 4561-3, (2011)

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Anticancer Properties of an Important Drug Lead Podophyllotoxin Can Be Efficiently Mimicked by Diverse Heterocyclic Scaffolds Accessible via One-Step Synthesis Magedov, I. V.; et al. J. Med. Chem. 54, 4234, (2011)

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Okundoperoxide, a bicyclic cyclofarnesylsesquiterpene endoperoxide from Scleria striatinux with antiplasmodial activity. Simon M N Efange et al J. Nat. Prod. 72, 280-3, (2009)

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Privileged structure-guided synthesis of quinazoline derivatives as inhibitors of trypanothione reductase. Andrea Cavalli et al Bioorg. Med. Chem. Lett. 19, 3031-5, (2009)

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?-Branched acyclic nucleoside analogues as inhibitors of Plasmodium falciparum dUTPase. Beatriz Baragaña et al Bioorg. Med. Chem. 19, 2378-91, (2011)

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Synthesis and antiprotozoal activities of dicationic bis(phenoxymethyl)benzenes, bis(phenoxymethyl)naphthalenes, and bis(benzyloxy)naphthalenes. Donald A Patrick et al Eur. J. Med. Chem. 44, 3543-51, (2009)

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Sarah Cannon Cancer Center Consensus Conference on Novel Developments with Podophyllotoxin Therapy. Semin. Oncol. 23(6 Suppl 13), 1-60, (1996)

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Podophyllotoxin in the treatment of genital warts. Beutner KR Curr. Probl. Dermatol. 24, 227-32, (1996)

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Merck 14,7546

Beil. 19,V,10,666

Aldrich MSDS 1, 1507:A / Corp MSDS 1 (2), 2857:B / FT-IR 2 (2), 2900:A / FT-IR 1 (2), 320:A / FT-NMR 1 (2), 1304:A / IR-Spectra (3), 1042:E / IR-Spectra (2), 911:G / RegBook 1 (2), 1937:I / Sigma FT-IR 1 (1), 572:D / Structure Index 1, 311:B:7

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